title: Enantioselective Friedel-Crafts alkylation of indoles with trifluoroethylidene malonates by copper-bis(oxazoline) complexes: construction of trifluoromethyl-substituted stereogenic tertiary carbon center.
abstract: An enantioselective alkylation of indoles with trifluoroethylidene malonates catalyzed by copper(II)-bis (oxazoline) complexes has been developed. The expected adducts with a stereogenic tertiary carbon center bearing a trifluoromethyl group were obtained in excellent yields (up to 99%) and ee values (up to 96% ee). The synthetic utility of this asymmetric catalytic reaction was demonstrated by the preparation of β-CF(3)-tryptophan and 4-CF(3)-β-carboline in high ee.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Rd., Shanghai, 200032, China.
authors.forename: Lele
authors.initials: L
authors.lastname: Wen
authors.forename: Qilong
authors.initials: Q
authors.lastname: Shen
authors.forename: Xiaolong
authors.initials: X
authors.lastname: Wan
authors.forename: Long
authors.initials: L
authors.lastname: Lu
mesh_terms: D000478:Alkylation; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D008314:Malonates; D002244:Carbon; D003300:Copper